IMPPAT Phytochemical information: 
7alpha-Acetoxyroyleanone

7alpha-Acetoxyroyleanone
Summary

SMILES: CC(=O)O[C@@H]1C[C@H]2C(C)(C)CCC[C@@]2(C2=C1C(=C(C(C)C)C(=O)C2=O)O)C
InChI: InChI=1S/C22H30O5/c1-11(2)15-18(24)16-13(27-12(3)23)10-14-21(4,5)8-7-9-22(14,6)17(16)20(26)19(15)25/h11,13-14,24H,7-10H2,1-6H3/t13-,14+,22+/m1/s1
InChIKey: MNEJUZVNGNCLJU-QLEMLULZSA-N
DeepSMILES: CC=O)O[C@@H]C[C@H]CC)C)CCC[C@@]6C=C%10C=CCC)C))C=O)C6=O))))O))))C
Scaffold Graph/Node/Bond level: O=C1C=CC2=C(C1=O)C1CCCCC1CC2
Scaffold Graph/Node level: OC1CCC2CCC3CCCCC3C2C1O
Scaffold Graph level: CC1CCC2CCC3CCCCC3C2C1C
Functional groups: CC(=O)OC; CC1=C(O)C(=C(C)C(=O)C1=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Diterpenoids
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Abietane diterpenoids
Synonymous chemical names:
7-acetylhorminone, 7alpha-acetoxyroyleanone,, 7alpha-acetoxyroyleanone
External chemical identifiers:
CID:CID_2751796
Chemical structure download


7alpha-Acetoxyroyleanone
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 374.48
Log P RDKit 4.07
Topological polar surface area (Å2) RDKit 80.67
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 3
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3


7alpha-Acetoxyroyleanone
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.447577


7alpha-Acetoxyroyleanone
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.56
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.94
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes